Sodium Carbonate → Methyl 5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypicolinate

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, to a solution of methyl 5-bromo-6-isobutoxypicolinate (698 mg), 2-fluoro-5-methoxyphenylboronic acid (454 mg), tris(dibenzylideneacetone)dipalladium(0) (65 mg) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (117 mg) in toluene (10 mL) was added 2.0 M aqueous sodium carbonate solution (2.67 mL), and the mixture was stirred at 100° C. for 30 min. The reaction mixture was filtered through celite, and water was added at room temperature. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (594 mg) as a pale-yellow oil.

Provenance & Evidence